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WO2010044342A1 - Élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique, élément électroluminescent organique blanc, dispositif d'affichage et dispositif d'éclairage - Google Patents

Élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique, élément électroluminescent organique blanc, dispositif d'affichage et dispositif d'éclairage Download PDF

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WO2010044342A1
WO2010044342A1 PCT/JP2009/066910 JP2009066910W WO2010044342A1 WO 2010044342 A1 WO2010044342 A1 WO 2010044342A1 JP 2009066910 W JP2009066910 W JP 2009066910W WO 2010044342 A1 WO2010044342 A1 WO 2010044342A1
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organic
compound
group
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transport layer
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秀雄 ▲高▼
善幸 硯里
利恵 片倉
秀謙 尾関
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Konica Minolta Inc
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Konica Minolta Inc
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Definitions

  • the present invention relates to an organic electroluminescence element, a method for producing an organic electroluminescence element, a white organic electroluminescence element, a display device, and an illumination device.
  • ELD electroluminescence display
  • inorganic electroluminescent elements and organic electroluminescent elements (hereinafter also referred to as organic EL elements).
  • organic electroluminescent elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic EL element has a configuration in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and injects electrons and holes into the light emitting layer to recombine excitons. It is an element that emits light by utilizing the emission of light (fluorescence / phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Therefore, it has a wide viewing angle, high visibility, and since it is a thin-film type completely solid element, it has attracted attention from the viewpoints of space saving and portability.
  • the organic EL device using phosphorescence emission is greatly different from the organic EL device using fluorescence emission, and the method for controlling the position of the emission center, particularly the emission layer, is particularly different.
  • An important technical issue in capturing the efficiency and lifetime of the device is how to recombine inside to stably emit light.
  • a multilayer stacked device having a hole transport layer (located on the anode side of the light emitting layer) and an electron transport layer (located on the cathode side of the light emitting layer) adjacent to the light emitting layer is better.
  • a hole transport layer located on the anode side of the light emitting layer
  • an electron transport layer located on the cathode side of the light emitting layer
  • Examples of electrode film formation by a wet process include using PEDOT / PSS in place of the ITO anode, applying low-melting metal paste (see, for example, Patent Document 1), and conductive paste material.
  • a cathode forming method by coating film formation (for example, see Patent Document 2) has been reported.
  • An object of the present invention is to provide an organic electroluminescence element having a high external extraction quantum efficiency, a long emission lifetime, and a low driving voltage, a white organic electroluminescence element including the element, a display device, and an illumination device. That is.
  • a phosphorescent organic EL device having an organic layer sandwiched between an anode and a cathode, It has an electron transport layer adjacent to the cathode as a constituent layer of the organic layer, and the electron transport layer is formed through a step of forming a film by a wet method and contains a low molecular weight compound or a non-conjugated high molecular weight compound
  • An organic electroluminescence device wherein the cathode is formed through a step of forming a film by a wet method using a conductive paste.
  • A represents —O—, —S— or —N (R1) —, and A11 to A18 each represents a nitrogen atom or —C (R2) —.
  • R1 and R2 each represent a bond, a hydrogen atom or a substituent. However, when there are a plurality of —C (R2) —, each —C (R2) — may be the same or different.
  • 4 The organic electroluminescence device as described in 2 or 3 above, wherein the compound represented by the general formula (1) has at least one pyridine ring as a partial structure.
  • Q1 represents a 5-membered or 6-membered aromatic ring.
  • Ar represents an aromatic hydrocarbon group or an aromatic heterocyclic group, and R3 and R4 represent a hydrogen atom or a substituent.
  • k represents an integer of 2 or 3, and has m secondary ligands L so as to satisfy the valence of iridium.
  • 11. 11 The organic electroluminescent device as described in 10 above, wherein the phosphorescent light emitting layer contains the compound represented by the general formula (1) as a light emitting host.
  • a film is formed by a wet method using a mixed solution or mixed dispersion of the compound represented by the general formula (1) and an alkali metal, alkaline earth metal, the alkali metal compound, or the alkaline earth metal compound.
  • a step of forming an electron transport layer by forming a film by a wet method using a coating liquid or dispersion containing the compound represented by the general formula (1), then alkali metal, alkaline earth metal, and the alkali metal And a step of impregnating the electron transport layer with a solution or dispersion containing the above compound or the alkaline earth metal compound, followed by a step of forming a cathode by a wet method using a conductive paste.
  • a white organic electroluminescence device comprising the organic electroluminescence device according to any one of 1 to 11 above.
  • a display device comprising the organic electroluminescent element according to any one of 1 to 11 or the white organic electroluminescent element according to 16.
  • An illumination device comprising the organic electroluminescent element according to any one of 1 to 11 or the white organic electroluminescent element according to 16.
  • an organic electroluminescence element having a high external extraction quantum efficiency, a long emission lifetime, and a low driving voltage, a white organic electroluminescence element including the element, a display device, and an illumination device. did it.
  • the compound for an organic EL device of the present invention has the structure according to any one of claims 1 to 11, and thereby has high external extraction quantum efficiency, long emission lifetime, and low driving voltage.
  • a luminescence element could be provided.
  • the organic EL device of the present invention is a phosphorescent organic EL device having an organic layer sandwiched between an anode and a cathode as described in claim 1, and the cathode is used as a constituent layer of the organic layer.
  • the electron transport layer is formed through a process of forming a film by a wet method, contains a low molecular weight compound or a non-conjugated high molecular weight compound, and the cathode is conductive.
  • It is an organic electroluminescence device that exhibits the effects described in the present invention (high external extraction quantum efficiency, long light emission lifetime, low driving voltage, etc.) by being formed through a process that uses a paste to form a film by a wet method. .
  • the cathode constituting the organic EL device of the present invention is formed by a wet process using a conductive paste, and an electron transport layer adjacent to the cathode (the cathode, anode, electron transport layer, etc. are described later)
  • the film is also formed by a wet method.
  • the low molecular weight compound according to the present invention refers to a compound having a value of 2,000 or less, which is obtained by directly measuring the relative mass (synonymous with molecular weight) of a molecule by mass spectrometry.
  • Mass spectrometry uses ionization methods such as EI, CI, FD, FAB, MALDI, ESI, etc., magnetic field deflection type, quadrupole type, ion trap type, time of flight (TOF) type, etc.
  • TOF time of flight
  • the low molecular weight compound according to the present invention is preferably a compound represented by the above general formula (1), and more preferably a compound represented by any one of the following general formulas (3) to (99).
  • the condensed aromatic heterocyclic ring represented by L is specifically acridine.
  • carbazole ring carboline ring, dibenzofuran ring, dibenzothiophene ring and the like are preferable.
  • these rings may have a substituent described later.
  • examples of the aromatic hydrocarbon ring represented by Q include a benzene ring, a biphenyl ring, and naphthalene.
  • Ring azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, naphthacene ring, triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, Examples include a fluoranthrene ring, a naphthacene ring, a pentacene ring, a perylene ring, a pentaphen ring, a picene ring, a pyrene ring, a pyranthrene ring, and an anthrathrene ring.
  • these rings may have a substituent described later.
  • the aromatic heterocycle represented by Q includes a furan ring, a thiophene ring, an oxazole ring. , Pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, indazole ring, benzimidazole ring, Benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, cinnoline ring, quinoline ring, isoquinoline ring, phthalazine ring, naphthyridine ring, carbazole ring, carboline ring, carboline ring, carboline ring, carboline ring, carboline ring
  • these rings may have a substituent described later.
  • L of the compound represented by the general formula (1) according to the present invention preferably has a partial structure represented by the general formula (2).
  • each of R1 and R2 is an alkyl group.
  • alkyl group e.g, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, hexyl, octyl, dodecyl, tridecyl, tetradecyl, pentadecyl, etc.
  • cycloalkyl groups eg, cyclopentyl
  • alkenyl group eg, vinyl group, allyl group, 1-propenyl group, 2-butenyl group, 1,3-butadienyl group, 2-pentenyl group, isopropenyl group, etc.
  • alkynyl group eg, Ethynyl group, propargyl group, etc.
  • aromatic hydrochloric acid e.g, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl,
  • substituents may be further substituted with the above substituents.
  • a plurality of these substituents may be bonded to each other to form a ring.
  • the compound represented by the general formula (1) according to the present invention preferably has at least one pyridine ring as a partial structure.
  • the low molecular weight compounds according to the present invention are disclosed in JP 2007-288035 A, Chem. Mater. It can be synthesized by referring to known methods described in 2008, 20, 5951, Experimental Chemistry Course 5th Edition (Edited by Chemical Society of Japan).
  • the non-conjugated high molecular weight compound according to the present invention refers to a compound having a number average molecular weight (Mw) of 1,000 or more in terms of standard polystyrene using a molecular weight measurement method using size exclusion chromatography (SEC).
  • Mw number average molecular weight
  • SEC size exclusion chromatography
  • the preferred molecular weight (Mw) for use in organic EL applications is 1,000 to 1,000,000.
  • GPC gel permeation chromatography
  • THF tetrahydrofuran
  • the conjugated system is a general term for molecular systems in which the ⁇ electrons of the multiple bond are delocalized due to the repetition of multiple bonds and single bonds.
  • the conjugated polymer means poly p-phenylene, polyacetylene, etc.
  • a non-conjugated polymer refers to a polymer material in which the polymer main chain does not mainly form a conjugated system (non-conjugated), such as polystyrene that does not have multiple bonds in the main chain or a polymer in which the main chain conjugated system is interrupted. and m-phenylene.
  • the low molecular weight compound and the non-conjugated high molecular weight compound according to the present invention are preferably used as an electron transport material constituting the electron transport layer of the organic EL device of the present invention, but in other organic layers of the organic EL device of the present invention. It may be contained.
  • the non-conjugated high molecular weight compound according to the present invention can be synthesized with reference to known methods described in the above-mentioned description relating to the synthesis of low molecular weight compounds and polymer synthesis / reaction (edited by the Society of Polymer Science). .
  • the low molecular weight compound and the non-conjugated high molecular weight compound according to the present invention are preferably used as an electron transport material constituting the electron transport layer of the organic EL device of the present invention, but in other organic layers of the organic EL device of the present invention. It may be contained.
  • the cathode (the cathode, anode, organic layer, etc. will be described in detail later) constituting the organic EL device of the present invention is formed by a wet method using a conductive paste.
  • the conductive paste according to the present invention preferably contains a conductive compound dispersion or a low melting point metal compound.
  • a conductive compound dispersion refers to a liquid material in a state where a conductive compound is dispersed in a liquid such as water or an organic solvent.
  • the conductive compound include metals and conductive polymer materials, and either an inorganic compound or an organic compound may be used.
  • the conductive compound is preferably used in a fine particle state (particle size is 1 nm to 10 ⁇ m) in order to facilitate the formation of a dispersion.
  • the organic solvent generally well-known solvents such as hydrocarbon solvents and fluorine-containing solvents can be appropriately used.
  • the conductive compound dispersion liquid is preferably a metal nanoparticle dispersion liquid.
  • the metal nanoparticle dispersion refers to a solution in which metal nanoparticles having an average particle diameter of 1 nm to 100 nm are suspended in a solvent.
  • a dispersion stabilizer, a protective agent or the like may be mixed in order to prevent reaggregation of metal nanoparticles.
  • the viscosity and the like can be adjusted by selecting the metal nanoparticle concentration and the type of solvent in accordance with the purpose of use and apparatus specifications.
  • Examples of the metal species of the metal nanoparticles related to the present invention include Ag, Au, Cu, Pd, Sn, In, Co, Bi, Al, and Zn.
  • the low melting point metal compound refers to an alloy having a melting point of 100 ° C. or lower, and the low melting point alloy is classified into an alkali metal type and other types depending on the use and handling.
  • Alkali metal is an alloy between alkali metals, and NaK is known. However, since it reacts violently with air and water, it is mainly used as a heat medium in a sealed state.
  • various alloys mainly containing zinc, indium, gallium, tin, bismuth, lead, etc. other than alkali metal are preferred.
  • solder that is an alloy of tin, galinstan that is a gallium alloy (composition is gallium 68.5%, indium 21.5%, tin 10%), wood metal that is a bismuth alloy (composition is 50% bismuth, lead 26 0.7%, tin 13.3%, cadmium 10%) and the like, and the melting point can be changed by changing the composition ratio of the alloy.
  • the conductive paste preferably contains an alkali metal, alkaline earth metal, alkali metal compound or alkaline earth metal compound.
  • the alkali metal according to the present invention represents an element excluding hydrogen among elements belonging to Group 1 (hydrogen, lithium, sodium, potassium, rubidium, cesium, francium) in the periodic table.
  • the alkaline earth metal according to the present invention represents a typical element (beryllium, magnesium, calcium, strontium, barium, radium) belonging to Group 2 of the periodic table.
  • the alkali metal compound or alkaline earth metal compound according to the present invention represents a salt, complex, oxide, or the like containing the alkali metal or alkaline earth metal element.
  • an alkali metal, an alkaline earth metal, a compound of the alkali metal or a compound of the alkaline earth metal is preferably contained at the interface between the electron transport layer and the cathode adjacent to the cathode.
  • the cathode contains an alkali metal, an alkaline earth metal, the alkali metal compound or the alkaline earth metal compound, or the electron transport layer contains an alkali metal, an alkaline earth metal, or the alkali metal. Or a compound of the alkaline earth metal.
  • an anode is fabricated by forming an electrode material, for example, a thin film made of an anode material on an appropriate substrate so as to have a thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • a thin film containing organic compounds such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer, which are element materials, is formed thereon.
  • the cathode and the electron transport layer adjacent to the cathode are applied and formed by a wet method.
  • the wet method there are a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method, an ink jet method, a printing method, a spray coating method, a curtain coating method, etc., but a precise thin film can be formed.
  • a method having high suitability for a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, or a spray coating method is preferable. Different film forming methods may be applied for each layer.
  • a thin film made of a cathode material is formed thereon so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm, and a desired organic EL device can be obtained by providing a cathode. .
  • the cathode, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode can be produced in the order of the reverse order.
  • a DC voltage When a DC voltage is applied to the multicolor display device obtained in this way, light emission can be observed by applying a voltage of about 2V to 40V with the positive polarity of the anode and the negative polarity of the cathode.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic EL device of the present invention it is preferable to produce from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light
  • the thickness of the light emitting layer is not particularly limited, but from the viewpoint of the uniformity of the film to be formed, the application of unnecessary high voltage during light emission, and the improvement of the stability of the emission color with respect to the drive current. It is preferable to adjust in the range of 2 nm to 200 nm, and more preferably in the range of 5 nm to 100 nm.
  • the light emitting layer of the organic EL device of the present invention preferably contains at least one of a light emitting host compound and a light emitting dopant as a guest material, and preferably contains a phosphorescent light emitting dopant described later as the light emitting dopant.
  • a light emitting layer of the organic EL device of the present invention it can be mentioned as an example of a preferable embodiment that a light emitting host compound and three or more kinds of light emitting dopants are contained.
  • a host compound also referred to as a light emitting host
  • a light emitting dopant also referred to as a light emitting dopant compound
  • the host compound in the present invention is a phosphorescent quantum yield of phosphorescence emission at a room temperature (25 ° C.) having a mass ratio of 20% or more in the compound contained in the light emitting layer. Is defined as a compound of less than 0.1.
  • the phosphorescence quantum yield is less than 0.01. Moreover, it is preferable that the mass ratio in a layer is 20% or more among the compounds contained in a light emitting layer.
  • the compound represented by the general formula (1) according to the present invention is also preferably used as the host compound according to the present invention.
  • known host compounds may be used alone or in combination of two or more. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient.
  • the light emitting host used in the present invention may be a conventionally known low molecular weight compound or a high molecular weight compound having a repeating unit, and a low molecular weight compound having a polymerizable group such as a vinyl group or an epoxy group (deposition polymerization property). Light emitting host).
  • a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • Luminescent dopant The light emitting dopant according to the present invention will be described.
  • the organic EL device of the present invention is phosphorescent, it contains at least a phosphorescent dopant (also referred to as phosphorescent emitter, phosphorescent compound, phosphorescent compound, etc.) as the luminescent dopant according to the present invention. To do.
  • a phosphorescent dopant also referred to as phosphorescent emitter, phosphorescent compound, phosphorescent compound, etc.
  • the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed. Specifically, it is a compound that emits phosphorescence at room temperature (25 ° C.) and has a phosphorescence quantum yield.
  • the phosphorescence quantum yield is preferably 0.1 or more, although it is defined as a compound of 0.01 or more at 25 ° C.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence emitting dopant according to the present invention achieves the above phosphorescence quantum yield (0.01 or more) in any solvent. It only has to be done.
  • phosphorescent dopants There are two types of light emission of phosphorescent dopants in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the host compound, and this energy is transferred to the phosphorescent dopant. Energy transfer type to obtain light emission from the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent dopant, and the phosphorescent dopant In any case, the excited state energy of the phosphorescent dopant is required to be lower than the excited state energy of the host compound.
  • the phosphorescent dopant can be appropriately selected from known materials used for the light emitting layer of the organic EL element.
  • the phosphorescent dopant according to the present invention is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound (platinum complex).
  • System compounds preferably iridium compounds, an osmium compound, or a platinum compound (platinum complex).
  • System compounds rare earth complexes, and most preferred are iridium compounds.
  • a compound represented by the above general formula (A) is preferably used.
  • the 5-membered or 6-membered aromatic ring represented by Q1 includes a benzene ring, an oxazole ring, an isoxazole ring, a thiophene ring, a furan ring, a pyrrole ring, a pyridine ring, a pyridazine ring, and a pyrimidine ring.
  • Pyrazine ring diazine ring, triazine ring, imidazole ring, pyrazole ring, triazole ring and the like.
  • the above ring may further form a condensed ring and may have a substituent.
  • the aromatic hydrocarbon group and the aromatic heterocyclic group represented by Ar are respectively -N (R1)-represented by A in the general formula (2), and A11 to A18.
  • -C (R2)-represented by each has the same meaning as the aromatic hydrocarbon group and aromatic heterocyclic group mentioned as examples of the substituent represented by R1 and R2.
  • the substituents represented by R3 and R4 are each represented by —N (R1) — represented by A in the general formula (2) and —C (R2) represented by A11 to A18. )-Has the same meaning as the substituents represented by R1 and R2.
  • oxycarboxylic acid for example, salicylaldehyde, oxyacetophenonate, etc.
  • dioxy compounds for example, biphenolate, etc.
  • diketones For example, acetylacetonato, dibenzoylmethanato, diethylmalonate, ethylacetoacetate, etc.
  • oxyquinones eg, pyromeconato, oxynaphthoquinato, oxyanthraquinato, etc.
  • tropolones eg, troponato, hinokitiolato, etc.
  • N-oxide compounds aminocarboxylic acids and similar compounds (eg, glycinato, alaninato, anthranilate, picolinato, etc.), hydroxylamines (eg, aminophenolato, ethanolaminato, mercap
  • ligands may also be used.
  • Nitrogen heterocyclic ligands for example, bipyridyl, phenanthroline, etc.
  • diketone ligands for example, bipyridyl, phenanthroline, etc.
  • the charge injection layer according to the present invention is provided as necessary, and includes an electron injection layer and a hole injection layer, and as described above, between the anode and the light emitting layer or the hole transport layer, and the cathode and the light emitting layer or the electron transport layer. It may be present between.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc. It is done.
  • the buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material having a function of transporting electrons and a very small ability to transport holes. By blocking the holes, the probability of recombination of electrons and holes can be improved.
  • the structure of the electron transport layer described later can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device according to the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer preferably contains the azacarbazole derivative mentioned as the host compound described above.
  • the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and can be obtained by the following method, for example.
  • Gaussian 98 Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • the ionization potential can be obtained as a value obtained by rounding off the second decimal place of the value (eV unit converted value) calculated by performing structural optimization using B3LYP / 6-31G *.
  • the reason why this calculated value is effective is that there is a high correlation between the calculated value obtained by this method and the experimental value.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy.
  • a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • the film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 nm to 100 nm, and more preferably 5 nm to 30 nm.
  • Charge transport layer electron transport layer, hole transport layer >> Examples of the charge transport layer according to the present invention include an electron transport layer and a hole transport layer.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
  • Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • No. 5,061,569 Having a condensed aromatic ring of, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the like.
  • NPD 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • JP-A-11-251067, J. Org. Huang et. al. A so-called p-type hole transport material described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used. In the present invention, these materials are preferably used from the viewpoint of obtaining a light emitting element with higher efficiency.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the thickness of the hole transport layer is preferably in the range of 5 nm to 5 ⁇ m, more preferably 5 nm to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • a hole transport layer having such a high p property because a device with lower power consumption can be produced.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided as a single layer or a plurality of layers.
  • an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
  • any material can be selected and used from among conventionally known compounds. For example, nitro-substituted fluorene derivatives, diphenylquinone derivatives Thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • the central metals of these metal complexes are In, Mg, Cu , Ca, Sn, Ga, or Pb can also be used as an electron transport material.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
  • the electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • the film thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • n-type electron transport layer doped with impurities examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 ⁇ m or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness is preferably in the range of 10 nm to 1000 nm, more preferably in the range of 10 nm to 200 nm, although it depends on the material.
  • cathode As the cathode, a material having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof as an electrode material is used.
  • Electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • these electrode substances are used as a conductive paste to form a thin film by a wet method to produce a cathode.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is preferably in the range of 10 nm to 5 ⁇ m, more preferably in the range of 50 nm to 200 nm.
  • the emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 nm to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • substrate As a substrate (hereinafter also referred to as a base, a base material, a support substrate, a support, etc.) that can be used in the organic EL device according to the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. Or opaque. When extracting light from the substrate side, the substrate is preferably transparent. Examples of the transparent substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, cyclone resins such as Arton (trade name, manufactured by JSR) or Appel (trade
  • an inorganic film, an organic film, or a hybrid film of both may be formed on the surface of the resin film.
  • a high barrier property film having a degree of 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ MPa) or less and a water vapor permeability of 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less is preferable.
  • the material for forming the barrier film may be any material that has a function of suppressing the intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction efficiency at room temperature of light emission of the organic EL device according to the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the organic EL element can be thinned.
  • the polymer film measured oxygen permeability by the method based on JIS K 7126-1987 is 1 ⁇ 10 -3 ml / m 2 / 24h or less, as measured by the method based on JIS K 7129-1992 water vapor transmission rate (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) is preferably that of 1 ⁇ 10 -3 g / (m 2 / 24h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • an inorganic or organic layer as a sealing film by covering the electrode and the organic layer on the outer side of the electrode facing the substrate with the organic layer interposed therebetween, and in contact with the substrate.
  • the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • the method for forming these films is not particularly limited.
  • vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
  • a vacuum is also possible.
  • a hygroscopic compound can also be enclosed inside.
  • Examples of the hygroscopic compound include metal oxides (eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.), perchloric acids (eg perchloric acid) Barium, magnesium perchlorate, and the like), and anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • metal oxides eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt
  • a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the substrate with the organic layer interposed therebetween or on the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by providing light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on a side surface of an organic EL element (Japanese Patent Laid-Open No. 1-220394), a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the substrate and the light emitter (Japanese Patent Laid-Open No.
  • a method of introducing a flat layer having a structure Japanese Patent Laid-Open No. 2001-202827, a method of forming a diffraction grating between any one of the substrate, the transparent electrode layer and the light emitting layer (including between the substrate and the outside world) No. 283751) That.
  • these methods can be used in combination with the organic EL device according to the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate A method of forming a diffraction grating between any layers of the transparent electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of 1.5 or less, more preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any one of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device according to the present invention is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or in combination with a so-called condensing sheet, for example, with respect to a specific direction, for example, the light emitting surface By condensing in the front direction, the luminance in a specific direction can be increased.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 ⁇ m to 100 ⁇ m.
  • the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.
  • the organic EL element according to the present invention is a white element
  • the display device of the present invention comprises the organic EL element of the present invention.
  • the display device of the present invention may be single color or multicolor, but here, the multicolor display device will be described.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, or the like.
  • the method is not limited, but preferred examples include vapor deposition, ink jet, spin coating, and printing.
  • the configuration of the organic EL element included in the display device is selected from the above-described configuration examples of the organic EL element as necessary.
  • the manufacturing method of an organic EL element is as having shown in the one aspect
  • a DC voltage When a DC voltage is applied to the obtained multicolor display device, light emission can be observed by applying a voltage of about 2V to 40V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state.
  • the alternating current waveform to be applied may be arbitrary.
  • the multicolor display device can be used as a display device, a display, and various light sources.
  • a display device or display full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.
  • Display devices and displays include televisions, personal computers, mobile devices, AV devices, teletext displays, information displays in automobiles, and the like. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc.
  • the present invention is not limited to these examples.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. It is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and the pixels for each scanning line respond to the image data signal by the scanning signal.
  • the image information is sequentially emitted to scan the image and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A has a wiring unit including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels 3 on the substrate.
  • the main members of the display unit A will be described below.
  • the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details are illustrated). Not)
  • the pixel 3 When the scanning signal is applied from the scanning line 5, the pixel 3 receives the image data signal from the data line 6 and emits light according to the received image data.
  • a full color display can be achieved by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a schematic diagram of a pixel.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • a full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.
  • the capacitor 13 is charged according to the potential of the image data signal, and the drive transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.
  • the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 maintains the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. Until then, the light emission of the organic EL element 10 continues.
  • the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the light emission of the organic EL element 10 is performed by providing the switching transistor 11 and the drive transistor 12 which are active elements with respect to the organic EL element 10 of each of the plurality of pixels. It is carried out.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good.
  • the potential of the capacitor 13 may be held continuously until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • the present invention not only the active matrix method described above, but also a passive matrix light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned.
  • FIG. 4 is a schematic view of a passive matrix display device.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the pixel 3 connected to the applied scanning line 5 emits light according to the image data signal.
  • the lighting device of the present invention will be described.
  • the illuminating device of this invention has the said organic EL element.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • the purpose of use of the organic EL element having such a resonator structure is as follows.
  • the light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However, It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the drive method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method.
  • a full-color display device can be manufactured by using two or more organic EL elements of the present invention having different emission colors.
  • the organic EL material of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by color mixing.
  • the combination of a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or two using the relationship of complementary colors such as blue and yellow, blue green and orange, etc. The thing containing the light emission maximum wavelength may be used.
  • a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light. Any of those combined with a dye material that emits light may be used, but in the white organic EL device according to the present invention, only a combination of a plurality of light-emitting dopants may be mixed.
  • an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is also improved.
  • the elements themselves are luminescent white.
  • luminescent material used for a light emitting layer For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known luminescent materials may be selected and combined to whiten.
  • CF color filter
  • the non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a glass substrate having a thickness of 300 ⁇ m is used as a sealing substrate, and an epoxy-based photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material.
  • LC0629B is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and an illumination device as shown in FIGS. Can be formed.
  • FIG. 5 shows a schematic diagram of a lighting device, and the organic EL element 101 of the present invention is covered with a glass cover 102 (in the sealing operation with the glass cover, the organic EL element 101 is brought into contact with the atmosphere. And a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more).
  • FIG. 6 shows a cross-sectional view of the lighting device.
  • 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • Example 1 Solution stability during preparation of coating solution ⁇
  • BCP, PBD, BAlq and the compound (11 types) according to the general formula (1) of the present invention which are materials used as the constituent material of the electron transport layer of the organic electroluminescence device of the present invention.
  • the solution stability of was evaluated.
  • the solvent is selected from five general solvents shown in Table 1 based on the solvent classification such as nonpolar aliphatic hydrocarbon, nonpolar aromatic hydrocarbon, polar aprotic, polar protic, and fluorine. I went there.
  • test sample 10 mg test sample was weighed, 1 ml of solvent was added, and the mixture was stirred at room temperature with a magnetic stirrer. After stirring for 30 minutes, when an insoluble matter could be visually confirmed, the mixture was heated and stirred at 50 ° C. for 30 minutes.
  • Evaluation conditions were purity measurement by HPLC (High Performance Liquid Chromatography) before and after standing at 25 ° C. for 24 hours.
  • Measuring device name High-performance liquid chromatograph LC-2000Plus series (manufactured by JASCO Corporation) Column: GL Science Co., Ltd. Inert Sil SIL-100A (4.6 ⁇ x250mm) Measurement conditions: Toluene / cyclohexane mixed solvent system (50/50 to 30/70) Evaluation was performed by the following rank evaluation.
  • Table 1 shows that the solution prepared using the compound represented by the general formula (1) according to the present invention exhibits very excellent solution stability.
  • the compounds of Sample Nos. 1 to 11 are highly versatile and very excellent as wet-type film-forming materials because they are dissolved in a plurality of solvent systems and exhibit high solution stability. all right.
  • Example 2 Manufacture of organic EL element 1-1 >> Patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ⁇ 100 mm ⁇ 1.1 mm glass substrate as a positive electrode on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate was formed, and then this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a solution prepared by dissolving 40 mg of BH-16 and 2 mg of ID-4 in 2.5 ml of dehydrated mesitylene was formed by spin coating at 1000 rpm for 30 seconds. Heat-dried at 150 degreeC for 1 hour, and provided the light emitting layer with a film thickness of 40 nm.
  • a solution prepared by dissolving 30 mg of HS-69 and 3 mg of cesium fluoride in 6 ml of dehydrated 1,1,1-3,3,3-hexafluoroisopropanol was spun on this light emitting layer under conditions of 1000 rpm and 30 seconds.
  • a film was formed by a coating method. Heat-dried at 120 ° C. for 1 hour to provide an electron transport layer having a thickness of 20 nm.
  • Organic EL element 1-1 was produced in the same manner except that Poly-1 which is a non-conjugated polymer electron transporting material was used instead of HS-69 used for the electron transport layer. 2 and the organic EL device 1-3 was produced in the same manner except that the cathode was directly formed without providing the electron transport layer on the light emitting layer.
  • the external quantum efficiency also referred to as light emission efficiency
  • the light emission lifetime and the drive voltage of the organic EL element 1-1 being 100, respectively.
  • the external quantum efficiency, light emission lifetime, and drive voltage of 2 are 105, 60, and 95, respectively
  • the external quantum efficiency, light emission lifetime, and drive voltage of the organic EL element 1-3 are 80, 1, 170, respectively.
  • Each of the organic EL elements 1-1 and 1-2 having an excellent performance as compared with the organic EL element 1-3 having no electron transporting layer has an electron transporting property in the phosphorescent organic EL element. It is clear that the layer has an important role.
  • Example 3 Manufacture of organic EL element 2-1 >> Patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ⁇ 100 mm ⁇ 1.1 mm glass substrate as a positive electrode on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate was formed, and then this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • HT-24 and 10 mg of HT-26 were dissolved in 3 ml of dehydrated toluene, and a film was formed by spin coating using this solution under conditions of 1000 and 30 seconds.
  • UV irradiation 100 W UVA, 200 mJ
  • photopolymerization / crosslinking 15 seconds
  • further heat drying 120 ° C. for 10 minutes to effect insolubilization by polymerizing polymerizable groups, resulting in a film thickness of 20 nm
  • the second hole transport layer was formed.
  • a solution prepared by dissolving 40 mg of BH-16 and 2 mg of ID-4 in 2.5 ml of dehydrated mesitylene was formed into a film by spin coating under conditions of 1000 rpm and 30 seconds. Heat-dried at 1 degreeC for 1 hour, and provided the light emitting layer with a film thickness of 40 nm.
  • a solution prepared by dissolving 30 mg of HS-70 in 6 ml of dehydrated 1,1,1-3,3,3-hexafluoroisopropanol was formed by spin coating at 1000 rpm for 30 seconds. Heat-dried at 120 ° C. for 1 hour to provide an electron transport layer having a thickness of 20 nm.
  • a solution prepared by dissolving 20 mg of potassium fluoride in 1 ml of methanol is dropped on the electron transport layer, spin coating is initially performed at 100 rpm for 10 seconds, and then immediately at 3000 rpm for 30 seconds. Potassium halide immersion was performed.
  • ⁇ Luminescent life> When driving at a constant current of 2.5 mA / cm 2 in a dry nitrogen gas atmosphere at 23 ° C., the time required for the luminance to drop to half of the luminance immediately after the start of light emission (initial luminance) was measured. The half-life time ( ⁇ 0.5 ) was used as an index of life. Similarly, a spectral radiance meter CS-1000 (manufactured by Minolta) was used for the measurement.
  • ⁇ Drive voltage> The voltage at the start of light emission was measured at a temperature of 23 ° C. in a dry nitrogen gas atmosphere. In addition, the voltage value at the time of the brightness
  • Table 2 shows the results obtained.
  • relative evaluation was performed by setting the external quantum efficiency, light emission lifetime, and driving voltage of the organic EL element 2-4 to 100, and Table 2 shows the results.
  • the effect of the present invention obtained by providing an electron transport layer (high external extraction quantum efficiency) It is clear that the electron transport layer is indispensable in the organic EL device using phosphorescence emission since the long emission lifetime and the low driving voltage are lower than those using the phosphorescence emission dopant. It is.
  • Example 4 Preparation of organic EL element 3-8 >> Patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ⁇ 100 mm ⁇ 1.1 mm glass substrate as a positive electrode on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate was formed, and then this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a solution prepared by dissolving 40 mg of BH-16 and 2 mg of ID-4 in 2.5 ml of dehydrated mesitylene was formed by spin coating at 1000 rpm for 30 seconds. Heat-dried at 150 degreeC for 1 hour, and provided the light emitting layer with a film thickness of 40 nm.
  • a solution prepared by dissolving 30 mg of HS-42 in 6 ml of dehydrated 1,1,1-3,3,3-hexafluoroisopropanol was formed by spin coating at 1000 rpm for 30 seconds. . Heat-dried at 120 ° C. for 1 hour to provide an electron transport layer having a thickness of 20 nm.
  • the above dispersion was discharged and patterned using an inkjet head (manufactured by Epson; MJ800C), and then baked at 120 ° C. for 5 minutes under nitrogen to form a silver cathode having a thickness of 110 nm. Manufactured.
  • organic EL elements 3-1 to 3-7 and 3-9 to 3-24 were changed in the same manner except that the constituent material of the electron transport layer (also referred to as electron transport material) was changed as shown in Table 3. 9 to 3-24 were produced respectively.
  • the lower light-emitting layer flowed out when the electron transport layer was applied, and the element could not be manufactured.
  • the organic EL device of the present invention in which the compound represented by the general formula (1) according to the present invention is contained in the electron transport layer as an electron transport material has a high external extraction quantum efficiency and a long emission lifetime. It is also clear that the driving voltage is low.
  • Example 5 Preparation of organic EL element 4-1 >> Patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) on which a 100 nm ⁇ 100 mm ⁇ 1.1 mm glass substrate as a positive electrode on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate was formed, and then this ITO transparent electrode was provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a solution prepared by dissolving 40 mg of BH-16 and 2 mg of ID-4 in 2.5 ml of dehydrated mesitylene was formed by spin coating at 1000 rpm for 30 seconds. Heat-dried at 150 degreeC for 1 hour, and provided the light emitting layer with a film thickness of 40 nm.
  • a solution prepared by dissolving 30 mg of HS-42 in 6 ml of dehydrated 1,1,1-3,3,3-hexafluoroisopropanol was formed by spin coating at 1000 rpm for 30 seconds. . Heat-dried at 120 ° C. for 1 hour to provide an electron transport layer having a thickness of 20 nm.
  • the obtained paste was set in a dispenser, discharged and patterned while being heated to 100 ° C., a cathode was formed, and an organic EL element 4-1 was manufactured.
  • Relative evaluation was performed by setting the external quantum efficiency, light emission lifetime, and drive voltage of the organic EL element 4-1 to 100.
  • the external quantum efficiency, light emission lifetime, and drive of the organic EL element 4-2 lacking the electron transport layer were obtained.
  • the voltages were 69, 5, and 200, respectively, and the importance of the electron transport layer in the phosphorescent organic EL device became clear.
  • Example 6 Provide of full-color display device> (Blue light emitting organic EL device) The organic EL element 2-1 described in Example 2 was used.
  • Green light-emitting organic EL device A green light-emitting organic EL element 2-1G was produced in the same manner as in the organic EL element 2-1 produced in Example 2, except that ID-4 was changed to PD-1.
  • red light-emitting organic EL element 2-1R was produced in the same manner as in the organic EL element 2-1 produced in Example 2, except that ID-4 was changed to PD-10.
  • the red, green and blue light-emitting organic EL elements are juxtaposed on the same substrate to produce an active matrix type full-color display device having the form shown in FIG. 1, and FIG. 2 shows the display of the produced display device. Only the schematic diagram of part A is shown.
  • a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate, and a plurality of juxtaposed pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.)
  • the scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a lattice shape and are connected to the pixels 3 at the orthogonal positions ( Details are not shown).
  • the plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data.
  • Example 7 Preparation of white light emitting lighting device ⁇
  • a white light-emitting organic EL element 2-1W was manufactured in the same manner as in the manufacture of the organic EL element 2-1 of Example 2, except that ID-4 was changed to PD-1, PD-10, and ID-4.
  • the obtained organic EL element 2-1W was covered with a glass case on the non-light emitting surface to obtain a lighting device.
  • the lighting device can be used as a thin white light emitting lighting device that emits white light having a low driving voltage, high external quantum efficiency (also referred to as light emission efficiency), and a long light emission lifetime.

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Abstract

L'invention porte sur un élément électroluminescent organique ayant un rendement quantique d'extraction externe élevé et une longue durée de vie d'émission de lumière tout en nécessitant une faible tension d'attaque. L'invention porte également sur un élément électroluminescent organique blanc, sur un dispositif d'affichage et sur un dispositif d'éclairage comprenant l'élément.
PCT/JP2009/066910 2008-10-15 2009-09-29 Élément électroluminescent organique, procédé de fabrication d'élément électroluminescent organique, élément électroluminescent organique blanc, dispositif d'affichage et dispositif d'éclairage Ceased WO2010044342A1 (fr)

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